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可可碱

可可碱用途

Theobromine 是在可可豆中发现的甲基黄嘌呤,可以抑制腺苷受体 A1 (AR1) 信号传导。

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可可碱名称

[ CAS 号 ]:
83-67-0

[ 中文名 ]:
可可碱

[ 英文名 ]:
Theobromine

[中文别名 ]:

[英文别名 ]:

3,7-Dimethyl-xanthine
Diurobromine
1H-Purine-2,6-dione, 3,7-dihydro-3,7-dimethyl-
EINECS 201-494-2
Teobromin
Theostene
2,6-Dihydroxy-3,7-dimethyl-purine
Theobromine
Diuretin
Thesal

可可碱生物活性

[ 描述 ]:

Theobromine 是在可可豆中发现的甲基黄嘌呤,可以抑制腺苷受体 A1 (AR1) 信号传导。

[ 相关类别 ]:

信号通路 >> G 蛋白偶联受体/G 蛋白 >> 腺苷受体

天然产物 >> 生物碱

研究领域 >> 神经疾病

[ 靶点 ]

Human Endogenous Metabolite

[体外研究]

浓度高于25μM的可可碱可降低这些细胞中的脂质积累。细胞活力不受可可碱的影响。可可碱在浓度高于25μM时抑制PPARγ,C /EBPα和脂肪形成基因的蛋白质表达。可可碱[1]也降低了这些基因的mRNA水平。

[体内研究]

可可碱组的体重低于载体组。此外,可可碱抑制了附睾和肾周脂肪组织的重量增加。可可碱组的平均脂肪细胞面积小于载体组[1]。当考虑每粪便重量的细菌数量时,可可碱组显示出比其他组更低的计数(分别与参考(RF)和可可(CC)组相比p = 0.021和p = 0.055)。可可饮食导致的pH值高于RF和CC饮食后的pH值。实验饮食不会显着影响乳酸的粪便浓度(RF组为4.26±1.54 mM; CC组为1.96±0.41 mM;可可碱组为2.69±0.73 mM)[2]。

[激酶实验]

将3T3-L1前脂肪细胞与MG132（10μM）预温育30分钟，然后在可可碱（25μM）存在或不存在下与IBMX一起温育8小时。将细胞在变性细胞提取缓冲液（50mM Tris-HCl，pH 7.5，含有70mMβ-巯基乙醇和2％SDS）中于95℃裂解10分钟。用稀释缓冲液（20mM Tris-HCl，pH 7.5，含有150mM NaCl，1mM EDTA，1mM EGTA，1％TritonX-100,2.5mM焦磷酸钠和蛋白酶抑制剂混合物）将细胞裂解物稀释20倍并在37℃下离心。 20,000克，持续30秒。将上清液与兔多克隆抗C /EBPβIgG，抗FLAG IgG或对照IgG在4℃温育过夜，然后与30μL蛋白G-Sepharose树脂在4℃温育1小时。用裂解缓冲液洗涤树脂三次，通过SDS-PAGE分离与树脂结合的蛋白质，并通过蛋白质印迹分析[1]。

[动物实验]

在该研究中使用Lewis大鼠（3周龄）。将大鼠随机分成三个饮食组（每组n = 7）：参照（RF）组摄取标准饮食AIN-93M，可可（CC）组摄取标准饮食，含10％天然Forastero可可含0.25％可可碱和可可碱（TB）组摄取了标准饮食，包括0.25％的可可碱，即可可碱在CC饮食中的含量[2]。

[参考文献]

[1]. Mitani T, et al. Theobromine suppresses adipogenesis through enhancement of CCAAT-enhancer-binding protein β degradation by adenosine receptor A1.

[2]. Martín-Peláez S, et al. Effect of cocoa's theobromine on intestinal microbiota of rats. Mol Nutr Food Res. 2017 Oct;61(10).

[相关活性小分子]

可可碱物理化学性质

[ 密度 ]:
1.6±0.1 g/cm3

[ 沸点 ]:
495.5±37.0 °C at 760 mmHg

[ 熔点 ]:
345-350 °C

[ 分子式 ]:
C₇H₈N₄O₂

[ 分子量 ]:
180.164

[ 闪点 ]:
253.5±26.5 °C

[ 精确质量 ]:
180.064728

[ PSA ]:
72.68000

[ LogP ]:
-2.08

[ 外观性状 ]:
白色至黄色结晶粉末

[ 蒸汽压 ]:
0.0±1.3 mmHg at 25°C

[ 折射率 ]:
1.737

[ 储存条件 ]:
Refrigerator

[ 水溶解性 ]:
slightly soluble,

可可碱MSDS

详细MSDS(安全技术说明书)

可可碱毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XH2275000

CHEMICAL NAME :: Theobromine

CAS REGISTRY NUMBER :: 83-67-0

BEILSTEIN REFERENCE NO. :: 0016464

LAST UPDATED :: 199701

DATA ITEMS CITED :: 40

MOLECULAR FORMULA :: C7-H8-N4-O2

MOLECULAR WEIGHT :: 180.19

WISWESSER LINE NOTATION :: T56 BN DN FNVMVJ B1 F1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human

DOSE/DURATION :: 26 mg/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay) Gastrointestinal - nausea or vomiting

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1265 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 837 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 552 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 530 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 300 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 200 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 11596 mg/kg/28D-C

TOXIC EFFECTS :: Endocrine - changes in thymus weight Related to Chronic Data - changes in testicular weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4172 gm/kg/49D-C

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - changes in testicular weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 23520 mg/kg/7W-C

TOXIC EFFECTS :: Behavioral - food intake (animal) Endocrine - changes in thymus weight Related to Chronic Data - changes in testicular weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 39900 mg/kg/19W-C

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - changes in testicular weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 40320 mg/kg/28D-C

TOXIC EFFECTS :: Endocrine - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 4 gm/kg/28D-C

TOXIC EFFECTS :: Cardiac - other changes

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 30400 mg/kg/43W-C

TOXIC EFFECTS :: Cardiac - other changes

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 33600 mg/kg/28D-C

TOXIC EFFECTS :: Behavioral - food intake (animal) Endocrine - changes in thymus weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 7500 mg/kg

SEX/DURATION :: male 49 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 17640 mg/kg

SEX/DURATION :: male 49 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 6300 mg/kg

SEX/DURATION :: female 1-21 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - live birth index (measured after birth) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 500 mg/kg

SEX/DURATION :: female 13 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 500 mg/kg

SEX/DURATION :: female 13 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - other developmental abnormalities

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3 gm/kg

SEX/DURATION :: female 6-29 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

MUTATION DATA

TEST SYSTEM :: Rodent - hamster

DOSE/DURATION :: 300 mg/kg

REFERENCE :: EXPEAM Experientia. (Birkhaeuser Verlag, POB 133, CH-4010 Basel, Switzerland) V.1- 1945- Volume(issue)/page/year: 38,600,1982 *** REVIEWS *** IARC Cancer Review:Human Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 51,421,1991 IARC Cancer Review:Animal No Available Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 51,421,1991 IARC Cancer Review:Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 51,421,1991 TOXICOLOGY REVIEW JRPMAP Journal of Reproductive Medicine. (2 Jacklynn Ct., St. Louis, MO 63132) V.3- 1969- Volume(issue)/page/year: 12,27,1974 TOXICOLOGY REVIEW FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 13,747,1989

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可可碱安全信息

[ 符号 ]:

GHS02, GHS06, GHS08

[ 信号词 ]:
Danger

[ 危害声明 ]:
H225-H301 + H311 + H331-H370

[ 警示性声明 ]:
P210-P260-P280-P301 + P310-P311

[ 个人防护装备 ]:
dust mask type N95 (US);Eyeshields;Gloves

[ 危害码 (欧洲) ]:
Xn:Harmful;

[ 风险声明 (欧洲) ]:
R22

[ 安全声明 (欧洲) ]:
S22-S24/25

[ 危险品运输编码 ]:
2811.0

[ WGK德国 ]:
1

[ RTECS号 ]:
XH2275000

[ 危险类别 ]:
6.1

[ 海关编码 ]:
2933990090

可可碱合成路线

详细合成路线

可可碱上下游产品

可可碱上游产品

可可碱下游产品

可可碱制备

1.将甲酰胺搅拌加热至170℃，加入4-氨基-5-甲酰胺基脲嗪，升温至180-185℃，反应半小时后降温至60℃，离心甩干，加水洗涤，得黄嘌呤。将其溶解于氢氧化钠溶液，升温至95℃，加活性炭，搅拌半小时后静置半小时，过滤。将滤液滴加到硫酸二甲酯中，控制pH8.2-8.5，35-38℃反应，加毕，搅拌15min，降温至28℃，调pH至9，静置4h，甩干、水洗，得可可碱。

2.由山茶的叶子或茎梗、可可的果实或果壳、可乐的种子用水或乙醇抽提后分离精制而得。

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可可碱海关

[ 海关编码 ]: 2933990090

[ 中文概述 ]:
2933990090. 其他仅含氮杂原子的杂环化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%

[ 申报要素 ]: 品名, 成分含量, 用途, 乌洛托品请注明外观, 6－己内酰胺请注明外观, 签约日期

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

可可碱文献

Cytochrome P450-dependent metabolism of caffeine in Drosophila melanogaster.

PLoS ONE 10(2) , e0117328, (2015)

Caffeine (1, 3, 7-trimethylxanthine), an alkaloid produced by plants, has antioxidant and insecticide properties that can affect metabolism and cognition. In vertebrates, the metabolites derived from ...

Multi-element, multi-compound isotope profiling as a means to distinguish the geographical and varietal origin of fermented cocoa (Theobroma cacao L.) beans.

Food Chem. 188 , 576-82, (2015)

Multi-element stable isotope ratios have been assessed as a means to distinguish between fermented cocoa beans from different geographical and varietal origins. Isotope ratios and percentage compositi...

Determination of phytochemicals, antioxidant activity and total phenolic content in Andrographis paniculata using chromatographic methods.

J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 995-996 , 101-6, (2015)

Antioxidant activity, total phenolics content and selected phytochemicals (alkaloids and andrographolides) were determined in Andrographis paniculata and in dietary supplements containing this plant. ...

更多文献

可可碱

可可碱用途

可可碱名称

可可碱生物活性

可可碱物理化学性质

可可碱MSDS

详细MSDS(安全技术说明书)

可可碱毒性和生态

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

可可碱安全信息

可可碱合成路线

详细合成路线

可可碱上下游产品

可可碱上游产品

可可碱下游产品

可可碱制备

可可碱海关

可可碱文献

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